


Day 4 Porn Star/Stripper AU

by arrowsshootyouforwards



Category: DC's Legends of Tomorrow (TV)
Genre: Anna is trying to be supportive, Len is a prostitute, M/M, Ray is a virgin
Language: English
Status: Completed
Published: 2016-04-30
Updated: 2016-04-30
Packaged: 2018-06-05 08:35:06
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,483
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6697561
Author URL: https://archiveofourown.org/users/arrowsshootyouforwards/pseuds/arrowsshootyouforwards
Summary: <blockquote class="userstuff">
              <p>Not quite Stripper or Porn Star but here goes:</p>
<p>Len is a prostitute and Ray is the 18 year old who hired him to take his virginity.</p>
            </blockquote>





	Day 4 Porn Star/Stripper AU

Day 4 Porn Star/Stripper AU

 

18 year old Ray refused to leave for college still a virgin, he would rather die. Well not die, maybe almost die? Never mind, anyway, he just couldn’t do it. Ray was tall, good looking, athletic, a jock at his high school, got the best grades and yet he was the only out gay kid in his school. Which meant there was really not much in the way of sexual exploration. His best friend, Anna felt for him. She knew what a hard time his father and brother gave him. Both were well known players and God forbid a Palmer graduate a virgin. He supposed that drastic times called for desperate measures.

“I’m going to do it,” he told Anna as they sat in AP Algebra.

“Do what?”

“I’m gonna lose my virginity, this weekend,” he told her determinedly.

“How Ray, our school has no other gay kids.”

“Anna I’m 18, I’m going to hire a prostitute,” he whispered.

“Isn’t that dangerous?”

“No, I found a totally legit escort agency. I’m just sick of my dad and brother lording it over me that I’m a virgin. My dad even said there’s no shame in paying for sex given my situation, he basically told me to do it.”

“Ray I don’t know,” Anna said softly.

“Everything will be fine, I just need you to cover for me, if anyone asks I got a fake ID and went to a gay bar in the city. Simple.”

“Ray why would people ask?”

“I mean my stupid brother. Also could I tell my dad I’m stopping over, you know how he gets when I ‘ _achieve’_ stuff.”

“Fine, but Ray, be careful. Please?”

“I will take every precaution, I promise.”

“And shower thoroughly before you come over, I don’t want you sleeping in my bed post sex with a stranger.”

“I will,” he laughed.

“And don’t do something stupid like fall in love with him.”

“Anna I’m not gonna fall in love with some guy I’m paying for sex,” Ray argued.

“I know that but, OK, never mind, let’s go off campus for lunch yeah? I want something… that won’t give me food poisoning.”

“Deal, I’ll drive, and you can help me pick someone from their website.”

“I am not involved in this.”

“Anna you’re my accomplice. My partner in crime, please? I trust your judgement.” He told her as the bell rang.

“OK, fine, I’m in, give me your phone.”

“Why my phone?”

“You are not using my laptop to look at hooker websites,” she told him firmly. “My mom knows how to check the deleted history.”

“OK, here, where do you wanna go, we have a free afternoon so we can go where ever. But… Guessing by the look on your face you want Big Belly Burger?”

“What else?”

“You know not everybody has the ability to eat and eat and not gain a pound.”

“Jealous?”

“Yeah, I am, eat in or drive through?”

“Drive through, we can go back to mine to look through the site, my parents are away all week and next.”

“You know if you need company you can come over anytime.”

“I know, I just don’t like to outstay my welcome.”

“Like you could,” he said pulling into the drive through, “my mom would have done anything for a daughter, you’re probably the closest thing she’ll ever have and she loves it.”

 “Really?”

“Seriously, in our family, you’re the favourite child.” He told her laughing.

“So how’re you paying for this weekend?”

“I put in a lot of extra hours in my grand-father’s auto shop.”

“Is that why you haven’t been free on weekends?”

“Kinda, plus when I wasn’t working I was at practice, studying, the gym or sleeping.”

“OK, let’s go pick the lucky fella.”

 

In Anna’s room they lounged on her bed, ate their burgers and looked at the website for the escort service. “Well see any you like?”

“I don’t know, I don’t even know what I like, how am I meant to pick a guy? You choose.”

“Ray I cannot pick a guy for you to fuck.”

“Please, you know me better than anyone, I trust you completely,” Ray told her.

“I don’t know Ray…” She told him.

“Please.”

“Fine, I’ll look, but you make the final decision.”

“Deal.”

 

Saturday morning Leonard Snart checked his online bookings for the day, four clients, three regulars who booked weeks in advance and one new. First he had a lady who worked in the mayor’s office as his PA, a stressful job, her needs were simple, mostly just letting off steam. Then he had two phone sessions booked which he could perform in his sleep. His first phone client was normally there in person but she was away with her family and hated her husband so much she couldn’t bare to go a week without speaking to Len over the phone if not in person. She mainly wanted company which he was happy to give her. It was like having a steady girlfriend he sometimes mused, if they got together they would do lunch, he’d cook and ask her about her day or they would go out, they sometimes stayed in and watched a movie, occasionally she’s want to get physical, to her it was all about the allusion of having an affair. His third client he could have a little fun with, a sweet little submissive who enjoyed being told what to do and praised. Again normally a client he saw in person but work had taken him out of the state so Len had given him his work Skype account and that would be how he kept tabs.

The fourth client, the newbie, had booked 8pm while late. Len texted his sister he would be home late and for her to order herself a pizza for dinner. Everything he was doing he did for Lisa, but she could never find out what he did. Because he knew she would feel guilty for it. After his first two clients Len had three hours to kill before his skype date. He texted Sara, asking her if she wanted to grab lunch if she wasn’t with a client.

“You got many bookings left today?” He asked.

“My last one should finish around 7, why?”

“I got an 8 while late, could you drop by and keep Lisa company for a few hours, she doesn’t do so well on her own since dad.”

“Sure, I can stop by. I thought you didn’t take those anymore?”

“I started accepting again, Lisa’s out-growing her skates and it’s competition season soon.”

“Well another season just opened up.”

“Baseball?” He asked confused.

“Virginity season.”

“Give over,” he told her eating his lunch.

“I took three last week alone, all 8 while late bookings. It’s that time when all the seniors are turning 18 and they don’t wanna go to college as virgins. I’m telling you, get tissues ready, you are gonna have a nervous 18 year old girl on the door step tonight.”

“Sara virginity season doesn’t exist.”

“How long since you did an 8 while late?”

“Since I got Lisa full time, so three years.”

“Exactly. You’re outta practice for this, you better make that first time good Len.”

“Sara I am not taking any virginities tonight or any night.”

“I will bet you, 50 bucks you take a virginity tonight.”

“OK, but you better have the cash by morning, because I’m not fucking a virgin.”

“Fine but Lenny, check her ID, last thing you want is to get set up.”

“I will check her ID, and that is it. And only my sister gets to call me Lenny. I gotta go, the office is sending Mick to look at the shower, a client got a little rough yesterday but Mick is gonna rip my balls off about it. Later.” Sara rolled her eyes and sipped her ice tea, her next client would be due soon so she decided to head off too. They shared a cab back to the building owned by the agency. Every escort had his or her own place which if they really wanted to, they could live in. Len knew several who did, but he couldn’t because of his sister.

 

Ray drove to the address given on the website and parked down the street. The doorman asked him to sign in, he used his real name, there didn’t really seem to be any good reason to hide it. In the elevator he bounced nervously on his heels, taking a deep breath to calm himself as he reached his floor.

Floor 9 Apartment C.

It was just past 8, so he took another deep breath and knocked on the door.

 

Leonard waited for his last client of the day, he called his sister to check on her, and he watched a movie as time ticked between clients. Finally it neared 8 so he took a shower, changed into fresh clothes as evening clients usually liked things a little more upscale and waited. Dimming the lights he listened, thinking about what Sara had said to him that day but shook his head dismissing the thought. He was not about to take the virginity of some girl.

_Knock knock._

He finished texting his sister that she should expect Sara to be over and left it in the kitchen. Opening the door he was momentarily surprised to see a young man rather than a woman but composed his surprise with a look of desire. “Hey there handsome, come on in.” He stepped back, allowing the guy into his home. “Just a formality here, can I see some ID?” He asked, he couldn’t really tell how old the guy was and Sara was right, better safe than sorry. The guy dug through his pockets pulling out his wallet and handing over his license. “All in order here, Raymond Palmer.”

“Just Ray actually, nobody calls me my full name, only my grandmother.” Len invited him to take a seat in the kitchen area, he did.

“No problem, so Ray what can I do for you tonight?” Len asked, his hands resting on and rubbing the young mans’ muscular shoulders. Ray hesitated, “no need to worry here Ray, I don’t judge, you can have whatever you want here,” Ray relaxed both physically and mentally and he began stammering out why he was here.

“Well, I would like to be- well not to be- Um, what I’m trying to say is please make me not a virgin? Anymore.” He said softly.

_Damn you Sara_ Len thought. “Of course I can,” he said softly, “tell me, how would you like this to go down? We can make it like you always pictured.” Len was playing a part, luckily the kid was one of the better looking clients he’s had the honor of deflowering over the years, so at least he could say there would be no performance issues.

“I guess I never really thought about it,” Ray mumbled embarrassed.

“How about this, my friend does a thing where she and the client pretend they’re on a date, watch a movie and then we move into the sex at your pace, how you feel comfortable. You set the rules, I play along. Sound good?” Ray nodded, smiling.

“Thank you.”

“You go pick a movie, I’ll set up a couple of things and I’ll make this a night you’ll be happy to remember.”

“Thank you, what can I call you?”

“Call me Len.”

“OK, Len.”

                                                                                                                                                                            

In the bedroom Len texted Sara asking her to stay with Lisa, he could be a while, he was thankful he didn’t work Sunday. He made the bed which he had changed the sheets from earlier, got out lube and condoms and melted some scented wax thing Sara had told him about. Apparently clients loved it, it improved the atmosphere or whatever. Returning to the living area he grabbed a bottle and two glasses from the kitchen before joining Ray on the couch where the menu screen of a DVD, he couldn’t tell what, was on screen. Pouring two glasses he handed one to Ray.

“Oh, um, I shouldn’t, I’m driving.”

“Don’t worry, it’s non-alcoholic, mainly just for the mood, you are underage and real alcohol causes issues with consent legalities. What’re we watching?”

“Um Jurassic World, it’s kinda a favourite.”

“No worries if it’ll help you relax it’s all up to you.”

“Sorry, um are there any ground rules?”

“Not really just the usual wear condoms, client is in charge and it’s all about consent.”

“So I can pretend we’re on an actual date right now?”

“Sure, whatever helps.”

“I’d like that.”

“Date treatment it is.”

“Can we cuddle?”

“Of course,” Len sipped his fake wine and placed the glass down, opening his arm for Ray to slide next to him and get comfortable, he pressed play on the movie.

“Can you like instigate things, I’m a little...”

“Sure, look don’t worry, once we get into it you’ll be having so much fun you’ll forget it’s your first time.” Len told him smiling and smoothing the kid’s hair.

The more of the movie they watched the more Len felt Ray relax against him he began making his move, starting with his fingers, dancing at the hem of Ray’s shirt, cautiously creeping beneath to trail up his bare skin, tracing shapes with his fingertips. Ray sighed against him, Len moved his face, lifting Ray’s chin with his other hand he brought their lips together. Ray’s lips were soft against his own as he shyly returned Len’s kiss. He deepened the kiss, Ray opening his mouth to allow Len access with his tongue, while Len’s free hand opened the top two buttons on Ray’s shirt. Feeling Ray turn towards him Len increased the pressure of his kisses, leaning back against the couch he encouraged Ray to move on top of him, he did, straddling Len, his knees framing Len’s thighs. Len continued to lead the kissing and Ray didn’t attempt to take the lead from him, he opened the rest of Ray’s shirt and Ray let it fall from his shoulders. Len broke the kiss to look at the body before him, perfectly toned abs, strong muscles. “You work out?” He asked running his hands over them admiringly.

“I play baseball and basketball, involves a lot of work out time.”

“Well I say go sports to that. Why don’t we move somewhere a little more comfortable?” Ray nodded, dipping his head for another kiss. Ray climbed off of Len who lead him by the hand to the bedroom. Len kicked his shoes off and Ray followed his lead, pulling off his sneakers and socks. Ray stood, unsure of what to do but Len sensed his hesitation and hooked his index fingers through the belt loops of the teenager’s jeans, pulling him over to the door, Len leaned against it, the bulge in the front of Ray’s jeans looked very promising but that was for later. Ray initiated a kiss this time and Len smiled into it, removing his own shirt in the process and opening his pants he let them drop to the floor, stepping out of them he remained in his boxer shorts. Pulling at Ray’s belt he pushed off the jeans, leaving them both in their underpants. “Let’s move this to the bed,” he said softly. Settling on the bed Len stopped Ray from kissing him, “now, very important question, would you like to top me or am I topping you?”

“Um, I never thought about that, um, you know what you’re doing, um, you top I wanna know how it feels.” Ray decided.

“If you change your mind at any point,” Len said trailing his hand down Ray’s chest and over the bulge in his pants, “just say the word.” Ray nodded against Len’s shoulder as Len rubbed his hard cock through his boxers.

“Oh fuck, that feels…”

“Good?” Ray nodded again as sigh escaping his lips. Len lifted his chin like before engaging Ray in another kiss, it was Ray this time who deepened it, climbing over Len’s thighs to straddling him again, “look at you getting brave,” Len smiled as Ray pulled back from the kiss. Len’s hands cupped Ray’s ass, massaging him through the fabric. “Think you’re ready to play with the big boys?”

“Very ready,” Ray said grinning he shuffled back to remove his underwear while Len gathered the bottle of lube from the nightstand. “How should I?”

“Hands and knees is easiest, for this part,” Len told him as he warmed the lube between his fingers, “just lay on your front to start, you’ll know what to do,” Len told him, “Just relax.” Len ran his dry hand over the curve of Ray’s ass. “Have you ever tried anything before?”

“I um, I’ve used my fingers a couple of times, but nothing bigger,” Ray replied.

“Good then this next part won’t feel so strange.” Len spread his cheeks apart and ran his lubed fingers over Ray’s hole, smiling as Ray lifted his hips a little. Len pulled his hips, so that Ray was on his knees, but hugging one of the pillows beneath him. “Stop holding your breath, just breathe,” Len said and talked Ray through stretching him, he added a second finger, surprising Ray, but in a good way. Len smirked as he heard Ray become more vocal, moaning as Len worked him open. Suddenly Ray clenched around him and swore loudly. “I’m guessing you never did that on your own?”

“Never, oh fuck, please do that again,” Ray begged and Len indulged him, determined to make him feel good. Slowly in worked in a third finger, Ray had never taken anything bigger than fingers, this was new territory for him. He began to feel Ray pushing back against his fingers.

“OK, I think you’re ready. Turn over,” he placed a pillow down, “lay on this, it’ll help,” he told him and removed his own underpants, and rolled on a condom. He watched as Ray stroked his cock while he waited, watching Len apply a generous amount of lube to his own cock before positioning himself between Ray’s knees. Len tested the waters with his fingers again, checking Ray was properly prepared before shifting closer and leaning over him, their cocks brushing together. “This is gonna feel strange at first, but remember to breathe, and if you want to stop you say the word, this is about you so no being a hero, OK?”

“OK,” Ray said softly, “could we kiss a little more? It was nice and it helped me relax earlier.”

“Of course we can,” Len smiled, lowering his lips to Ray’s. Ray relaxed against his lips, lifting his hips to show he was ready. Len placed his cock at Ray’s entrance and slowly pushed in, just past the head of his cock and paused to study the face beneath him. “Breathe Ray, come on,” he reminded him. “OK?” Ray nodded and Len pushed further in, pausing every now and then to let Ray adjust to him.

“Oh this is so different then fingers,” Ray murmured breathlessly.

“You’re doing really well,” Len encouraged, “almost got all of me right now.”

“Seriously?” Ray asked surprised, he’d gotten a good look at Len’s dick, it was big in both length and thickness. The thick he could certainly feel, it was the hot burn and stretch he was feeling, but he could hardly believe he was taking almost the whole length.

“Seriously, ready and this is all of it,” Len stopped, Ray could feel the skin of his balls against his ass and he believed it. “How’s it feel?”

“Weird,” Ray admitted.

“Good weird or?”

“Definitely a good weird,” Ray confirmed, “could you move a little, but um, take it slow?”

“Sure,” Len smiled and slowly withdrew his cock, he could see the struggle on Ray’s face but God was this difficult for him too. He’d not fucked a male virgin in years, he’d almost forgotten how good it felt to be inside the tight, intense heat, he knew he had to be careful, this was about Ray, not him. It took all his willpower not to let his primal urges take over and slam his hips into Ray. “You’re doing so well,” he praised still moving at a slow pace in and out of Ray, he kissed Ray again, staggering his movements, making Ray moan.

“Can you go a little faster?” Ray asked, sweat beading on his forehead. Len obliged, picking up the pace thrust by thrust. “Mm, fuck, stop,” Ray panted and Len froze.

“Are you OK?”

“I’m good, can we try a different position though?”

“Sure, um, why don’t you go on top, you can control it?” Ray nodded and sighed as Len pulled out of him and took the pillow from beneath him to stack up against the headboard with the others. Len leaned back against it, his cock up-straight against his stomach, his legs bent slightly at the knees. He beckoned Ray toward him and Ray once again found himself in this man’s lap. “OK, you ready?” Ray nodded and reached towards Len’s cock, Len was impressed, his grip was firm but not too tight as he pushed the cock towards his ass. “Take it easy, remember.” Ray nodded again and sank slowly onto Len’s cock pausing half way.

“Oh fuck,” he muttered dropping his forehead to Len’s shoulder, breathing heavily.

“Good weird again?”

“Amazing weird,” Ray replied.

“Alright, try moving a little, as great as this feels, for me, believe me when I say it’ll feel great for you.” Ray nodded and braced his hands on Len’s shoulders, and sank lower onto his cock. Then he tried something different. He tried rolled his hips, like he’d seen guys in porn movies do, Len seemed to get what he was trying and held his hips to guide him through the movement, which felt awesome. Ray loved the feel of Len’s hands on him, firmly at his waist, kneading his ass or carding through his hair he loved them. Ray could feel a ball of electricity pooling in his belly, knotting tighter every time he impaled himself on Len. He didn’t notice it, but he himself was becoming more and more vocal, cursing and moaning with every movement.

“Shit, I can feel it, I’m so close,” he said rolling his hips again. Len took initiative and wrapped his hand around Ray’s own neglected cock, smearing the pre-cum as a lubricant he jerked Ray off in time with his movements. Suddenly Ray’s hips stuttered and his head whipped back as he came over himself and Len, who guided his waist and stroked his cock through his orgasm. “Oh fuck that felt…” Ray trailed off resting against Len. Lifting himself out of Len’s lap he noticed Len about to remove the empty condom. “Wait you didn’t-“

“Not about me Ray, I’m fine.”

“No wait, I kinda wanna know what it feels like, to have someone cum inside you, obviously with the condom on, but please, I really wanna feel it.” Ray pleaded with him and though he normally wouldn’t, Len figured he could use a real release for once and not his hand. “Can I try on my front this time?”

“Sure, go ahead,” Ray turned over, hugging his pillow and presenting his ass to Len. Len poured a little more lube over his cock and sank into Ray from behind. He was careful because Ray was likely to be both sore and sensitive. Gently he knocked Ray’s knees apart to get a better angle on Ray and moved his hips in tight, quick movements. Ray moved to get more comfortable when he felt his prostate get hit.

“Ah fuck,” he could also feel his cock growing hard again. He loved being 18. With his hand he began stroking himself as Len increased his pace, always checking it was OK with Ray. Suddenly Ray’s ass clenched tight around his cock as Ray got a second orgasm, pushing Len over the edge that he came in the condom in thick spurts. As his breathing returned to normal he laid his body over Ray’s and pulled slowly out of him, moving quickly to dispose of the condom and collapse on the sheets. “I made a bit of a mess,” Ray said worried.

“Don’t worry, I’ll send the sheets to be washed, I don’t actually live here, it’ll be fine. Was that OK for you?” Len asked seriously.

“That was amazing for me. It felt so good and just wow, I may take to sleeping on my side or front for a couple of days though.” Len smiled.

“It’ll pass, just sit with a cushion for a day or two.”

“Thanks for the advice, um do you mind if I shower, is that OK?”

“Sure, there are towels in there, use whatever you need, I’ll clean up in here then wait in the lounge.”

“Thank you.”

Len pulled on his boxers and stripped the bed, gathering both their clothes into piles, dropping Ray’s underpants and jeans by the bathroom door. Ray was quick in the shower and re-dressed to go in search of his shirt. Len handed it to him and Ray pulled out his wallet with the envelope with the money he owed. “I hope it was all you wanted.”

“And more, um, would it be OK for me to book with you again sometime?” He asked shyly.

“If you really want to but I’m warning you, I do this for a living, you will never be the only one, don’t go getting feelings now.”

“I won’t,” Ray said, “it’s just college is still months away and I have a lot more firsts to try out and well, you made me feel safe, like it should feel. You made it good for me.”

“OK then, your choice, let me walk you out.” At the door Ray turned back suddenly.

“Could I get a kiss goodnight?” Len rolled his eyes but indulged him, pulling him by the shirt for one last heat filled kiss.

“Goodnight.”

“’Night,” Ray called cheerily as he retreated to the elevator.

 

Ray arrived back at Anna’s where she was waiting up for him, excited to hear how it went. “I’m booking him again,” he told her after describing his evening.

“Ray,” she warned.

“Not like that, his services were really good for the money I paid, he was good with me, understanding that I was inexperienced, why wouldn’t I want to explore more firsts with him?”

“Because you’re going to college soon and Ray I know you, you’ll catch feelings.”

“And I want to be ready. I’ll be fine, trust me on this, I won’t get feelings for him, he’s just my sex tutor.”

“OK,” Anna sighed, “I trust you.”


End file.
